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Details

Stereochemistry ACHIRAL
Molecular Formula C21H27N7O
Molecular Weight 393.4854
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of REVERSINE

SMILES

C1CCC(CC1)NC2=C3N=CNC3=NC(NC4=CC=C(C=C4)N5CCOCC5)=N2

InChI

InChIKey=ZFLJHSQHILSNCM-UHFFFAOYSA-N
InChI=1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)

HIDE SMILES / InChI

Molecular Formula C21H27N7O
Molecular Weight 393.4854
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18483302 https://www.ncbi.nlm.nih.gov/pubmed/22477067

First synthesized in 2004 by the group of Peter G. Schultz, reversine is a 2,6- diamino substituted purine showing a potent inhibition on Aurora B, a protein kinase overexpressed in a variety of solid tumors. Due to its relevance in the cell cycle regulation, Aurora B represents a good target for anti-cancer drug development, so that reversine can be used as a promising lead compound for new potential antitumor agents. Reversine is a potent human A3 adenosine receptor antagonist with Ki of 0.66 μM, and a pan-aurora A/B/C kinase inhibitor with IC50 of 12 nM/13 nM/20 nM, respectively. Reversine also inhibits Mps1. Reversine is effective in inhibiting the growth of thyroid cancer cells by cell cycle arrest or apoptosis, especially with the more aggressive ATC and PDTC. Apoptosis was induced by the mitochondria-independent pathway. Reversine is being under investigation in clinical therapeutics.

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
"Reversine" and its 2-substituted adenine derivatives as potent and selective A3 adenosine receptor antagonists.
2005 Jul 28
The 2,6-disubstituted purine reversine induces growth arrest and polyploidy in human cancer cells.
2007 Dec
Induction of growth arrest and polycomb gene expression by reversine allows C2C12 cells to be reprogrammed to various differentiated cell types.
2007 Dec
Reversine inhibits spontaneous synaptic transmission in cultured rat hippocampal neurons.
2007 Jun
Reversine stimulates adipocyte differentiation and downregulates Akt and p70(s6k) signaling pathways in 3T3-L1 cells.
2007 Jun 29
Detection and functional characterization of Pgp1 (ABCB1) and MRP3 (ABCC3) efflux transporters in the PLHC-1 fish hepatoma cell line.
2007 Mar 30
Reversine, a novel Aurora kinases inhibitor, inhibits colony formation of human acute myeloid leukemia cells.
2008 May
The Aurora B kinase activity is required for the maintenance of the differentiated state of murine myoblasts.
2009 Feb
Reversine increases the plasticity of lineage-committed cells toward neuroectodermal lineage.
2009 Jan 30
Proteomic signature of reversine-treated murine fibroblasts by 2-D difference gel electrophoresis and MS: possible associations with cell signalling networks.
2009 Jun
Proteomic analysis of blastema formation in regenerating axolotl limbs.
2009 Nov 30
Tumor cell-specific bioluminescence platform to identify stroma-induced changes to anticancer drug activity.
2010 Apr
Beneficial effects of reversine on in vitro development of miniature pig somatic cell nuclear transfer embryos.
2010 Apr
Reversine enhances generation of progenitor-like cells by dedifferentiation of annulus fibrosus cells.
2010 Apr
Cell reprogramming: expectations and challenges for chemistry in stem cell biology and regenerative medicine.
2010 Aug
Dissecting the role of MPS1 in chromosome biorientation and the spindle checkpoint through the small molecule inhibitor reversine.
2010 Jul 12
Ontology-based meta-analysis of global collections of high-throughput public data.
2010 Sep 29
Patents

Patents

Sample Use Guides

Mice: mice were orally fed with reversine 0.1 mg/kg or reversine 1.0 mg/kg
Route of Administration: Oral
In SW579 cells, G2/M phase arrest was found in low-dosage treatment (1 uM) with reversine. The levels of apoptosis (both early and late apoptosis) in ARO, WRO and SW579 cells with reversine (10 uM) treatment were SW579 > ARO> WRO, and were SW579 0 ARO>WRO with 1 or 5 uM reversine treatment.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:06:48 GMT 2023
Edited
by admin
on Fri Dec 15 18:06:48 GMT 2023
Record UNII
Z499CLJ023
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
REVERSINE
MI  
Common Name English
REVERSINE [MI]
Common Name English
2-(4-MORPHOLINOANILINO)-N6-CYCLOHEXYLADENINE
Systematic Name English
2-(4-MORPHOLINOANILINO)-6-CYCLOHEXYLAMINOPURINE
Systematic Name English
Code System Code Type Description
MESH
C484369
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
EVMPD
SUB129711
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
CAS
656820-32-5
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
FDA UNII
Z499CLJ023
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID8041113
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
MERCK INDEX
m9562
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB07340
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
WIKIPEDIA
REVERSINE
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
CHEBI
70723
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
SMS_ID
100000155657
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
PUBCHEM
210332
Created by admin on Fri Dec 15 18:06:48 GMT 2023 , Edited by admin on Fri Dec 15 18:06:48 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ANTAGONIST
IC50
Related Record Type Details
ACTIVE MOIETY